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5,5-Diphenylhydantoin

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Products Intro: Product Name:5,5-Diphenylhydantoin
CAS:57-41-0
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CAS:57-41-0
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CAS:57-41-0
Purity:90%+ Package:10mg, 25mg, 50mg, 100mg, Other scale please email Sales@pipitech.com Remarks:5,5-Diphenylimidazolidine-2,4-dione.
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Products Intro: Product Name:Phenytoin
CAS:57-41-0
Purity:0.99 Package:5KG;1KG Remarks:Large package please cotact us according to customer demand

Lastest Price from 5,5-Diphenylhydantoin manufacturers

  • 5,5-Diphenylhydantoin
  • US $1.00 / KG
  • 2020-01-13
  • CAS:57-41-0
  • Min. Order: 1KG
  • Purity: 98%-99.9%
  • Supply Ability: 100kg
5,5-Diphenylhydantoin Basic information
Description Generic formulation Indications Dose titration Plasma levels monitoring Cautions Interactions Special populations Behavioural and cognitive effects in patients with epilepsy Psychiatric use
Product Name:5,5-Diphenylhydantoin
Synonyms:5-Diphenylhydantoin;PHENYTOIN BASE;PHENYTION;PHENYTOIN;5,5-DIPHENYLHYDANTHOIN;5,5-DIPHENYLHYDANTOIN;5,5-DIPHENYL-2,4-IMIDAZOLIDINEDIONE;DIPHENYLHYDANTOIN
CAS:57-41-0
MF:C15H12N2O2
MW:252.27
EINECS:200-328-6
Product Categories:API's;Aromatics;Heterocycles;API intermediate
Mol File:57-41-0.mol
5,5-Diphenylhydantoin Structure
5,5-Diphenylhydantoin Chemical Properties
Melting point 293-295 °C(lit.)
Boiling point 395.45°C (rough estimate)
density 1.1562 (rough estimate)
refractive index 1.5906 (estimate)
Fp 11 °C
storage temp. 2-8°C
solubility DMSO: soluble
pkapKa 8.43(H2O,t =25,I=0.025) (Uncertain)
form Powder
color White to almost white
Water Solubility <0.01 g/100 mL at 19 ºC
Merck 14,7322
BRN 384532
Stability:Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.
InChIKeyCXOFVDLJLONNDW-UHFFFAOYSA-N
CAS DataBase Reference57-41-0(CAS DataBase Reference)
NIST Chemistry Reference5,5-Diphenylhydantoin(57-41-0)
EPA Substance Registry SystemPhenytoin (57-41-0)
Safety Information
Hazard Codes T,Xn,F
Risk Statements 45-61-22-63-40-39/23/24/25-23/24/25-11-20/21/22
Safety Statements 53-45-36/37-16-7
RIDADR 2811
WGK Germany 3
RTECS MU1050000
Autoignition Temperature550 °C
HazardClass 6.1(b)
PackingGroup II
HS Code 29332100
Hazardous Substances Data57-41-0(Hazardous Substances Data)
ToxicityLD50 in mice (mg/kg): 92 i.v.; 110 s.c. (Stille, Brunckow)
MSDS Information
ProviderLanguage
5,5-Diphenyl-2,4-imidazolidinedione English
SigmaAldrich English
ACROS English
ALFA English
5,5-Diphenylhydantoin Usage And Synthesis
DescriptionPhenytoin is a first- generation antiepileptic drug (AED) known with the proprietary brand name of Epanutin® (Pfizer, Tadworth) in the UK and Dilantin® (Pfizer, New York, NY) in the USA.
Generic formulationMHRA/ CHM advice to minimize risk when switching patients with epilepsy between different manufacturers’ products (incl. generic products):
  • Doctors are advised to ensure that their patients are maintained on a specific manufacturer’s product.
IndicationsEpilepsy
Monotherapy and adjunctive therapy of focal and generalized tonic- clonic seizures.

Recommendations summarized from NICE (2012)
  • Seizure types: on referral to tertiary care (focal seizures), contraindicated (generalized tonic- clonic seizures if there are absence or myoclonic seizures or if juvenile myoclonic epilepsy is suspected, absence seizures, myoclonic seizures).
  • Epilepsy types: on referral to tertiary care (benign epilepsy with centrotemporal spikes, Panayiotopoulos syndrome, late- onset childhood occipital epilepsy), contraindicated (absence syndromes, juvenile myoclonic epilepsy, idiopathic generalized epilepsy, Dravet syndrome).
Dose titrationEpilepsy
150–300 mg od or divided into two doses, then increased to 200– 500 mg daily (dose to be increased gradually as necessary, with plasma phenytoin concentration monitoring).
Plasma levels monitoringPhenytoin has a narrow therapeutic index and the relationship between dose and plasma. Phenytoin concentration is non- linear: small dosage increases in some patients may produce large increases in plasma concentration with acute toxic adverse effects. Similarly, a few missed doses or a small change in phenytoin absorption may result in a marked change in plasma phenytoin concentration. Monitoring of plasma phenytoin concentration improves dosage adjustments. The usual total plasma phenytoin concentration for optimum response is 0– 20 mg/ L (careful interpretation of total plasma phenytoin concentration is necessary in pregnancy, the elderly, and certain disease states where protein binding may be reduced and it may be more appropriate to measure free plasma phenytoin concentration).
CautionsPatients with acute porphyrias (contraindication).
InteractionsWith AEDs
  • Phenytoin is extensively bound to serum plasma proteins and is prone to competitive displacement. Phenytoin is metabolized by hepatic enzymes (cytochrome P450 CYP2C9 and CYP2C9) and is particularly susceptible to inhibitory drug interactions because it is subject to saturable metabolism.
  • Several AEDs, including eslicarbazepine, oxcarbazepine, topiramate, and valproate, potentially increase phenytoin serum levels.
  • Vigabatrin may decrease phenytoin plasma levels.
  • Carbamazepine, phenobarbital, and valproate may either increase or decrease phenytoin serum levels.
  • Phenytoin is a potent inducer of hepatic drug- metabolizing enzymes and may reduce the levels of drugs metabolized by these enzymes.
  • Phenytoin may alter serum levels and/ or effects of carbamazepine, lamotrigine, phenobarbital, and valproate.

With other drugs
  • Phenytoin serum levels are potentially increased by analgesic/ anti- inflammatory agents (such as azapropazone, phenylbutazone, salicylates), anaesthetics (halothane), antibacterial agents (such as chloramphenicol, erythromycin, isoniazid, sulfadiazine, sulfamethizole, sulfamethoxazoletrimethoprim, sulfaphenazole, sulfisoxazole, sulfonamides), antifungal agents (such as amphotericin b, fluconazole, itraconazole, ketoconazole, miconazole, voriconazole), antineoplastic agents (such as capecitabine, fluorouracil), psychotropic agents (such as chlordiazepoxide, diazepam, disulfiram, fluoxetine, fluvoxamine, methylphenidate, sertraline, trazodone, viloxazine), cardiovascular agents (such as amiodarone, dicoumarol, diltiazem, nifedipine, ticlopidine), H2- antagonists (such as cimetidine), HMG- CoA reductase inhibitors (such as fluvastatin), hormones (such as oestrogens), immunosuppressant drugs (such as tacrolimus), oral hypoglycaemic agents (such as tolbutamide), proton pump inhibitors (such as omeprazole).
  • Phenytoin plasma levels may be decreased by antibacterial agents (such as ciprofloxacin, rifampicin), antineoplastic agents (such as bleomycin, carboplatin, cisplatin, doxorubicin, methotrexate), antiulcer agents (such as sucralfate), antiretrovirals (such as fosamprenavir, nelfinavir, ritonavir), bronchodilators (such as theophylline), cardiovascular agents (such as reserpine), folic acid, hyperglycaemic agents (such as diazoxide), St John抯 wort (Hypericum perforatum).
  • Phenytoin serum levels may be either increased or decreased by antibacterial agents (such as ciprofloxacin), antineoplastic agents, and psychotropic agents (such as chlordiazepoxide, diazepam, and phenothiazines).
  • Phenytoin may alter serum levels and/ or effects of the following drugs: antibacterial agents (such as doxycycline, rifampicin, tetracycline), antifungal agents (such as azoles, posaconazole, voriconazole), antihelminthics (such as albendazole, praziquantel), antineoplastic agents (such as teniposide), antiretrovirals (such as delavirdine, efavirenz, fosamprenavir, indinavir, lopinavir/ ritonavir, nelfinavir, ritonavir, saquinavir), bronchodilators (such as theophylline), cardiovascular agents (such as digitoxin, digoxin, mexiletine, nicardipine, nimodipine, nisoldipine, quinidine, verapamil), coumarin anticoagulants (such as warfarin), ciclosporin, diuretics (such as furosemide), HMG- CoA reductase inhibitors (such as atorvastatin, fluvastatin, simvastatin), hormones (such as oestrogens, oral contraceptives), hyperglycaemic agents (such as diazoxide), immunosuppressant drugs, neuromuscular blocking agents (such as alcuronium, cisatracurium, pancuronium, rocuronium, vecuronium), opioid analgesics (such as methadone), oral hypoglycaemic agents (such as chlorpropamide, glyburide, tolbutamide), psychotropic agents (such as clozapine, paroxetine, quetiapine, sertraline), vitamin D.

With alcohol/food
Acute alcohol intake may increase phenytoin serum levels while chronic alcoholism may decrease serum levels. There are no specific foods that must be excluded from diet when taking phenytoin (phenytoin doses should be taken preferably with or after food).
Special populationsHepatic impairment
Reduce dose to avoid toxicity.

Renal impairment
Nil.

Pregnancy
  • Phenytoin may produce congenital abnormalities in the offspring of a small number of epileptic patients. Therefore, phenytoin should only be used during pregnancy, especially early pregnancy, if in the judgement of the physician the potential benefits clearly outweigh the risk.
  • In addition to the reports of increased incidence of congenital malformations, such as cleft lip/ palate and heart malformations in children of women receiving phenytoin, there have been reports of a foetal hydantoin syndrome, consisting of prenatal growth deficiency, micro- encephaly, and mental deficiency in children born to mothers who have received phenytoin. There have been isolated reports of malignancies, including neuroblastoma, in children whose mothers received phenytoin during pregnancy.
  • ?An increase in seizure frequency during pregnancy occurs in a proportion of patients, possibly due to altered phenytoin absorption or metabolism. Therefore, periodic measurement of serum phenytoin levels is particularly valuable in the management of a pregnant patient with epilepsy as a guide to an appropriate adjustment of dosage; however, postpartum restoration of the original dosage will probably be indicated.
  • Breast- feeding is not recommended for women taking phenytoin because phenytoin appears to be secreted in low concentrations in human milk.
Behavioural and cognitive effects in patients with epilepsyPhenytoin has an overall favourable behavioural profile, although it has been occasionally associated with negative effects on mood and psychotic symptoms (especially at higher doses). The cognitive profile is more problematic, especially in the attention and memory domains. Cognitive adverse effects associated with phenytoin are often dose- dependent and may be particularly obvious in visually guided motor functions.
Psychiatric usePhenytoin has no approved indications in psychiatry, although the results of small randomized studies have shown that it may be useful in the maintenance treatment of bipolar disorder, major depressive disorder, and impulsive aggression.
Chemical Propertieswhite crystals or powder
Chemical PropertiesPhenytoin is a crystalline compound
UsesReduces incidence of grand mal seizures; appears to stabilize excitable membranes perhaps through effects on Na+, K+, and Ca2+ channels.
UsesA sodium channel protein inhibitor
DefinitionChEBI: A imidazolidine-2,4-dione that consists of hydantoin bearing two phenyl substituents at position 5.
Brand nameAnticonvulsant. Dilantin (Pfizer) [Name previously used: Diphenylhydantoin.].
Biological FunctionsPhenytoin is a valuable agent for the treatment of generalized tonic–clonic seizures and for the treatment of partial seizures with complex symptoms. The establishment of phenytoin (at that time known as diphenylhydantoin) in 1938 as an effective treatment for epilepsy was more than simply the introduction of another drug for treatment of seizure disorders. Until that time the only drugs that had any beneficial effects in epilepsy were the bromides and barbiturates, both classes of compounds having marked CNS depressant properties. The prevailing view among neurologists of that era was that epilepsy was the result of excessive electrical activity in the brain and it therefore seemed perfectly reasonable that CNS depressants would be effective in antagonizing the seizures. Consequently,many patients received high doses of barbiturates and spent much of their time sedated. Also, since CNS depression was considered to be the mechanism of action of AEDs, the pharmaceutical firms were evaluating only compounds with profound CNS depressant properties as potential antiepileptic agents. It was, therefore, revolutionary when phenytoin was shown to be as effective as phenobarbital in the treatment of epilepsy without any significant CNS depressant activity. This revolutionized the search for new anticonvulsant drugs as well as immediately improving the day-to-day functioning of epileptic patients.
An understanding of absorption, binding, metabolism, and excretion is more important for phenytoin than it is for most drugs. Following oral administration, phenytoin absorption is slow but usually complete, and it occurs primarily in the duodenum. Phenytoin is highly bound (about 90%) to plasma proteins, primarily plasma albumin. Since several other substances can also bind to albumin, phenytoin administration can displace (and be displaced by) such agents as thyroxine, triiodothyronine, valproic acid, sulfafurazole, and salicylic acid.
General DescriptionFine white or almost white crystalline powder. Odorless or almost odorless. Tasteless.
Air & Water ReactionsInsoluble in water.
Reactivity Profile5,5-Diphenylhydantoin is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). 5,5-Diphenylhydantoin is incompatible with strong oxidizers and strong bases.
Fire HazardFlash point data for 5,5-Diphenylhydantoin are not available; however, 5,5-Diphenylhydantoin is probably combustible.
Clinical UsePhenytoin (Dilantin) was originally introduced for the control of convulsive disorders but has now also been shown to be effective in the treatment of cardiac arrhythmias. Phenytoin appears to be particularly effective in treating ventricular arrhythmias in children.
Phenytoin, like lidocaine, is more effective in the treatment of ventricular than supraventricular arrhythmias. It is particularly effective in treating ventricular arrhythmias associated with digitalis toxicity, acute myocardial infarction, open-heart surgery, anesthesia, cardiac catheterization, cardioversion, and angiographic studies.
Phenytoin finds its most effective use in the treatment of supraventricular and ventricular arrhythmias associated with digitalis intoxication. The ability of phenytoin to improve digitalis-induced depression of A-V conduction is a special feature that contrasts with the actions of other antiarrhythmic agents.
Clinical UsePhenytoin is one of very few drugs that displays zero-order (or saturation) kinetics in its metabolism.At low blood levels the rate of phenytoin metabolism is proportional to the drug’s blood 1evels (i.e., first-order kinetics). However, at the higher blood levels usually required to control seizures, the maximum capacity of drug-metabolizing enzymes is often exceeded (i.e., the enzyme is saturated), and further increases in the dose of phenytoin may lead to a disproportionate increase in the drug’s blood concentration. Since the plasma levels continue to increase in such a situation, steady-state levels are not attained, and toxicity may ensue. Calculation of half-life (t1/2) values for phenytoin often is meaningless, since the apparent half-life varies with the drug blood level.
Acute adverse effects seen after phenytoin administration usually result from overdosage. They are generally characterized by nystagmus, ataxia, vertigo, and diplopia (cerebellovestibular dysfunction). Higher doses lead to altered levels of consciousness and cognitive changes.
A variety of idiosyncratic reactions may be seen shortly after therapy has begun. Skin rashes, usually morbilliform in character, are most common. Exfoliative dermatitis or toxic epidermal necrolysis (Lyellís syndrome) has been observed but is infrequent. Other rashes occasionally have been reported, as have a variety of blood dyscrasias and hepatic necrosis.
Side effectsThe most common side effect in children receiving long-term therapy is gingival hyperplasia, or overgrowth of the gums (occurs in up to 50% of patients). Although the condition is not serious, it is a cosmetic problem and can be very embarrassing to the patient. Hirsutism also is an annoying side effect of phenytoin, particularly in young females. Thickening of subcutaneous tissue, coarsening of facial features, and enlargement of lips and nose (hydantoin facies) are often seen in patients receiving long-term phenytoin therapy. Peripheral neuropathy and chronic cerebellar degeneration have been reported, but they are rare.
There is evidence that phenytoin is teratogenic in humans, but the mechanism is not clear. However, it is known that phenytoin can produce a folate deficiency, and folate deficiency is associated with teratogenesis. Only a few well-documented drug combinations with phenytoin may necessitate dosage adjustment. Coadministration of the following drugs can result in elevations of plasma phenytoin levels in most patients: cimetidine, chloramphenicol, disulfiram, sulthiame, and isoniazid (in slow acetylators). Phenytoin often causes a decline in plasma carbamazepine levels if these two drugs are given concomitantly.
Ethotoin and mephenytoin are congeners of phenytoin that are marketed as AEDs in the United States. They are not widely used.
Side effectsThe rapid IV administration of phenytoin can present a hazard. Respiratory arrest, arrhythmias, and hypotension have been reported.
Safety ProfileConfirmed carcinogen producing lymphoma, Hodgkin's disease, tumors of the skin and appendages. Experimental carcinogenic and tumorigenic data. A human poison by ingestion. Poison experimentally by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Moderately toxic by an unspecified route. Experimental teratogenic and reproductive effects. Human systemic effects by ingestion: dermatitis, change in motor activity (specific assay), ataxia (loss of muscle coordmation), degenerative brain changes, encephalitis, hallucinations, dtstorted perceptions, irritabihty, and jaundice. Human teratogenic effects by ingestion: developmental abnormalities of the central nervous system, carlovascular (circulatory) system, musculoskeletal system, craniofacial area, skin and skin appendages, eye, ear, other developmental abnormalities. Effects on newborn include abnormal growth statistics (e.g., reduced weight gain), physical abnormakties, other postnatal measures or effects, and delayed effects. Human mutation data reported. A drug for the treatment of grand mal and psychomotor seizures. When heated to decomposition it emits toxic fumes of NOx
Potential ExposurePhenytoin is an amide pharmaceutical used in the treatment of grand mal epilepsy, Parkinson’s syndrome; and in veterinary medicine. Human exposure to phenytoin occurs principally during its use as a drug. Figures on the number of patients using phenytoin are not available, but phenytoin is given to a major segment of those individuals with epilepsy. The oral dose rate is initially 100 mg given 3 times per day and can gradually increase by 100 mg every 24 weeks until the desired therapeutic response is obtained. The intravenous dose is 200350 mg/day.
Drug interactionsPlasma phenytoin concentrations are increased in the presence of chloramphenicol, disulfiram, and isoniazid, since the latter drugs inhibit the hepatic metabolism of phenytoin. A reduction in phenytoin dose can alleviate the consequences of these drug–drug interactions.
CarcinogenicityPhenytoin and its sodium salt are reasonably anticipated to be human carcinogens based on sufficient evidence from studies in experimental animals.
ShippingUN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3249 Medicine, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
Purification MethodsCrystallise the hydantoin from EtOH. [Beilstein 24 III/IV 1748.]
IncompatibilitiesIncompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Similar organic amides react with azo and diazo compounds, releasing toxic gases. Contact with reducing agents can release flammable gases. Amides are very weak bases but they can react as acids, forming salts. Mixing amides with dehydrating agents such as phosphorus pentoxide or thionyl chloride generates the corresponding nitrile.
PrecautionsPhenytoin either should not be used or should be used cautiously in patients with hypotension, severe bradycardia, high-grade A-V block, severe heart failure, or hypersensitivity to the drug.
Because of the increase in A-V transmission observed with phenytoin administration, it should not be given to patients with atrial flutter or atrial fibrillation. Phenytoin will probably not restore normal sinus rhythm and may dangerously accelerate the ventricular rate.
5,5-Diphenylhydantoin Preparation Products And Raw materials
Raw materialsBenzaldehyde
Preparation Products2,4,6-Trifluorophenol
Tag:5,5-Diphenylhydantoin(57-41-0) Related Product Information
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